February 19, 2025

Building with Fearlessness, Leadership Wisdom from Calibrate Founder, Isabelle Kenyon

This week on Unfinished Business, we sat down with our dear friend Isabelle Kenyon, the founder of Calibrate, for an incredibly candid conversation about building (and scaling!) in healthcare, raising massive rounds of capital, and finding your way through intense pressure as a solo founder.

Isabelle's journey into healthcare startups began with a deeply personal experience - she broke her back skiing, leading to a frustrating 10-month recovery journey that opened her eyes to the gaps in our healthcare system. As she told us, "I am one of the most connected people in New York City, I have access to the best healthcare on planet earth, and I can't figure this out."

That experience sparked a mission to fix healthcare delivery, eventually leading her to found Calibrate. But what really caught our attention was her raw honesty about the pressures of rapid growth. When we asked about raising $100M in just one year, instead of feeling on top of the world, Isabelle shared: "I felt awful every day. Like I felt like I was having a fire hose sprayed in my face every morning. I felt like I wasn't the right person. Like I felt like I had no idea what I was doing."

For those wondering about going solo as a founder - Isabelle had fascinating thoughts about why she chose not to have a co-founder, having worked at three startups with single founders before Calibrate. As she put it, "I don't want to learn the dynamics of co-founders while starting a business." (Though she did admit to being a bit jealous of our partnership when things got tough!)

Want to hear more about Isabelle's journey, including her thoughts on the future of metabolic health and GLP-1s? [Listen to the full episodehere. Trust us - you won't want to miss her insights on everything from fundraising to finding your way through the pressures of hypergrowth.

P.S. If you know any amazing single men, Isabelle is still looking! (Lee couldn't resist adding this - she's already got one successful matchmaking story under her belt!)

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